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Caribbean vacation rentals

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Top-rated vacation rentals in Caribbean

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Hut in Bavaro
Rekindle a Romance in a Retro Thatched Hut on the Beach
We also have another two house very similar next door. Get back to basics in a grass-roofed hut surrounded by palm trees and sand. Spend days sunbathing on a deck, mesmerized by the endless blue horizon. Interior furnishings are mostly locally crafted and perfectly compliment the bohemian off-grid vibe. We personally deliver the house giving extensive information about the area and the house. Varied breakfast is included and you will find it in fridge and wardrobes for you to do it to your liking. Wifi, bicycles, barbecue, beach games, amacas, etc...
$186 per night
Condo in Montego Bay
Jus' Beachy! Luxury Apt in a B/front Gated Cmnty.
This new beach theme apartment is located in 22 Freeport – A gated community in Freeport Montego Bay. 22 Freeport is a beach front complex on a Marina that features 24 hour security, a gym, infinity edge pool and playground; whilst the unit on the ground floor opens onto a cozy back yard space that flows into an open green space. Be sure to check out my 2nd listing in this community "Jus' Beachy Deux" on my profile if your dates are not available here or if you would like to book both units.
$194 per night
Villa in Lake Worth
Bliss Villa 4 w/Heated Pool +BEST Rate & Location!
Welcome to Lake Worth Beach's coolest vacation rental. This million+ dollar property boasts an amazing courtyard with a HEATED pool, dining nooks, lounge chairs, grill, outdoor shower & cabana BA - all surrounded by 4 private villas. Recently renovated *Villa 4 is perfect for those who want to walk to downtown cafes/nightlife/parks AND also be near a beautiful beach. Villa 4 is an accessible space w/king bed, work desk w/1Gig Internet, washer/dryer, kitchen, central AC, & on-site parking.
$280 per night

Caribbean beach vacation rentals

Home in North Side
Ocean's Edge: Beachfront Home with Rooftop Views
$695 per night
Villa in Treasure Beach
Villa Elia~Private Seafront Tropical Paradise
$800 per night
Cottage in Tortola
BVI Village - Villas of Tortola's bohemian retreat
$675 per night
Home in Isabela
Oceanfront Hideaway Main Floor
$161 per night
Home in Marathon
100' Dockage, Pool, Kayaks, Paddle Board, Bikes!
$550 per night
Villa in Kralendijk
Villa Shores 32, private stunning oceanfront villa
$833 per night
Hotel room in Rincon
Tres Sirenas Boutique Hotel Oceanfront Suite
$358 per night
Home in Grand Cayman
Pools of the Kai #3 by Grand Cayman Villas
$588 per night
Condo in Collectivity of Saint Martin
Paradise vacation on La Plage
$157 per night
Tiny home in Rincón
Tree of Life🌿 Private Pool Tiny House in Rincon!!
$194 per night
Private room in La Habana
Casa Blanca B&B with beautiful terrace &sea views
$37 per night
Serviced apartment in Punta Cana
Punta Cana Ocean View - Luxury Bavaro Beachfront!
$538 per night

Caribbean house rentals

Home in Las Terrenas
Amazing sea view luxury modern, fully staffed
$515 per night
Home in Fort Lauderdale
LUX House /Heated Spa- Downtown & Beach
$497 per night
Home in Key West
Grand Home/Heated, Salt Water Pool/Dog Friendly
$445 per night
Home in Grand Cayman
Kai Tana by Grand Cayman Villas
$700 per night
Home in San Cayetano de Venecia
Quinta La Ceiba Modern Home with Pool in DairyFarm
$200 per night
Home in Cape Coral
Completely Remodeled 3 Bedroom Home With A Pool
$180 per night
Home in Lauderdale-by-the-Sea
Heated Pool! Massive Yard+Walk To Beach & Shops!
$608 per night
Home in Cartagena
Super Luxury 7 Bedroom House in the Old City
$927 per night
Home in La Caña
Modern house with pool and jacuzzi in Playa Nueva Romana with fast internet
$252 per night
Home in Aguadilla Pueblo
Ta-Vera Oasis
$200 per night
Home in Hollywood
Private jungle hideaway w/pool-close to beach!
$342 per night
Home in Port Charlotte
Escape to Heated Pool | 3 King Beds | Private Home
$362 per night

Beach house rentals in Caribbean

Home in St. Thomas
Stunning Water Views
$650 per night
Home in Bathsheba
Caribbean Chic Beach House on the East Coast
$288 per night
Home in Upper Sugarloaf Key
Pink Beach Paradise
$725 per night
Home in Luquillo
La orilla beach house
$798 per night
Private room in Cruz Bay
Hawk's Rest
$135 per night
Home in Naples
Island lifestyle family vacation home (Salt Pool)
$492 per night
Home in Marco Island
Luxury 4 Bedroom House ⭐️ Heated Pool ⭐️ Near Beach
$850 per night
Home in Río Grande
$875 per night
Home in Cap-Haitien
$170 per night
Home in Fort Lauderdale
Waterfront luxury. Sleeps 6 adults and 4 children.
$748 per night
Home in Isabela
Costa Bonita Beach House /With Solar System
$255 per night
Home in Grand Cayman
Castaway Cove by Grand Cayman Villas
$812 per night

Your guide to Caribbean

All About the Caribbean

The Caribbean is made up of 26 island countries surrounded by bejeweled blue and green waters and is known around the world as a holiday paradise. People flock here, especially in the winter, for warm sands, golden sunshine, and that sense of island time abandon — plus, the fruity drinks under towering palm trees. The Dominican Republic is the most visited of all the islands due to its vibrant city and cultural life and postcard-perfect beaches. West of that is Cuba, famous for its Old World architecture, rich jazz and music scenes, and several UNESCO World Heritage Sites. Closer to South America is little St. Lucia, known for its rainforests, colorful coral reefs (perfect for diving and snorkeling), and, of course, pristine beaches surrounded by the island’s volcanic peaks.

The countries in the Caribbean are extremely diverse, not only in their histories, cultures, and languages, but their landscapes and topographies. For example, vibrant Jamaica could not be more different from super-chill Aruba and swanky St. Barts. So whether you’re seeking an island that’s large or small, glitzy or low-key, in the Caribbean there is a sanctuary for everyone.

When is the best time to stay in a vacation rental in Caribbean?

Thanks to trade winds, the weather in the Caribbean is sunny and pleasant all year round. The only caveat is that tropical storms and hurricanes occur to varying degrees of intensity here, and their likelihood increases from about July to November. But it’s the dry season from December through March that makes the region so popular. Villas to rent in the Caribbean are in demand during the winter, as many feel the urge to escape the colder weather up north and take in the sun, fun, and the many festivals — like Trinidad’s Carnival, the biggest of the Caribbean’s carnivals, and the Bahamas’ Junkanoo, a cultural street festival and celebration dating back centuries that takes place between Boxing and New Year’s Day. There are also plenty of Caribbean rentals in May and June, if you don’t mind the chance of a little rain.

What are the top things to do in Caribbean?

Santo Domingo

Santo Domingo, the capital of the Dominican Republic, is the oldest continuously inhabited colonial settlement in the Western Hemisphere and was founded in 1496. The historic city center, Zona Colonial, is a UNESCO World Heritage Site, with cobblestone streets, colorful houses, and colonial-style architecture and structures like the 16th-century Basilica Cathedral of Santa María la Menor, the oldest surviving cathedral in the Americas.


Sitting off the coast of Venezuela is the Dutch island of Curaçao, lesser known than its neighbors, but with just as much to offer — including its lack of hurricane seasons. Willemstad, the capital, is one of the few UNESCO World Heritage cities in the Caribbean, and it’s pulsing with nightlife and festivals like Carnival and King’s Day. The diving here is top-notch, there are dozens of stunning beaches to choose from, and the lodging ranges from hostels to five-star resorts — so there’s something here for everyone.

Reggae in Jamaica

Jamaica is the birthplace of reggae. The music took off in the late 1960s, and by the 1970s, with the superstardom of Bob Marley and the Wailers, it became known throughout the world. If you’re in Kingston, check out the clubs, still playing the dub style that made the genre so popular. The best of the best musicians have been known to play at the annual reggae festival held in June.